bromo-difluoro-(3,4,6-tri-O-benzyl-α-D-lyxo-hexopyranosid-2-ulosyl)methane

Base Information

• Chemical Name: bromo-difluoro-(3,4,6-tri-O-benzyl-α-D-lyxo-hexopyranosid-2-ulosyl)methane
• CAS No.: 944733-25-9
• Molecular Formula: C₂₈H₂₇BrF₂O₅
• Molecular Weight: 561.42

Synonyms:bromo-difluoro-(3,4,6-tri-O-benzyl-α-D-lyxo-hexopyranosid-2-ulosyl)methane

Chemical Property of bromo-difluoro-(3,4,6-tri-O-benzyl-α-D-lyxo-hexopyranosid-2-ulosyl)methane

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

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Technology Process of bromo-difluoro-(3,4,6-tri-O-benzyl-α-D-lyxo-hexopyranosid-2-ulosyl)methane

There total 2 articles about bromo-difluoro-(3,4,6-tri-O-benzyl-α-D-lyxo-hexopyranosid-2-ulosyl)methane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 41.0%

dibromodifluoromethane (75-61-6) + 1,5-anhydro-2,3,4,6-tetra-O-benzyl-D-lyxo-hex-1-enitol (138511-92-9) → bromo-difluoro-(3,4,6-tri-O-benzyl-α-D-lyxo-hexopyranosid-2-ulosyl)methane (944733-25-9)

Guidance literature:

With triethyl borane; In hexane; N,N-dimethyl-formamide; at 20 ℃; for 6h;

DOI:10.1021/ol070835f

Reference yield:

phenyl-2,3,4,6-tetra-O-benzyl-1-seleno-β-D-galactopyrannoside (139903-48-3,139903-49-4,143995-67-9) → bromo-difluoro-(3,4,6-tri-O-benzyl-α-D-lyxo-hexopyranosid-2-ulosyl)methane (944733-25-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / i-Pr₂NEt; t-BuOOH; Ti(Oi-Pr)4 / CH₂Cl₂; hexane / 3 h / 0 °C

2: 41 percent / BEt₃ / dimethylformamide; hexane / 6 h / 20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; triethyl borane; N-ethyl-N,N-diisopropylamine; In hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol070835f

Reference yield: 68.0%

bromo-difluoro-(3,4,6-tri-O-benzyl-α-D-lyxo-hexopyranosid-2-ulosyl)methane (944733-25-9) → bromo-difluoro-(3,4,6-tri-O-benzyl-α-D-galactopyranosyl)methane (1308272-18-5)

Guidance literature:

With aluminum isopropoxide; In isopropyl alcohol; Reflux; Inert atmosphere;

DOI:10.1002/chem.201100183

upstream raw materials:

dibromodifluoromethane

1,5-anhydro-2,3,4,6-tetra-O-benzyl-D-lyxo-hex-1-enitol

phenyl-2,3,4,6-tetra-O-benzyl-1-seleno-β-D-galactopyrannoside

Downstream raw materials:

C₃₀H₃₂F₂O₆

C₃₉H₄₇F₂NO₉

C₃₉H₄₉F₂NO₉

2,3,4-tri-N,O,O-acetyl-1,1-difluoro-1-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-galactopyranosyl)-3-amino-4-hydroxy-butan-2-ol

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